1-(bromomethyl)-4-chloro-2-methoxybenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared by substituting 1-bromomethyl-4-chloro-2-methoxy-benzene and 3-[1,3,2]dioxaborinan-2-yl-pyridine for 1-bromomethyl-4-chloro-2-methoxy-benzene and 4-pyridyl boronic acid, respectively, in Example 700A. MS (ESI) m/e 234 (M+H)+.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared by substituting 1-bromomethyl-4-chloro-2-methoxy-benzene and 3-[1,3,2]dioxaborinan-2-yl-pyridine for 1-bromomethyl-4-chloro-2-methoxy-benzene and 4-pyridyl boronic acid, respectively, in Example 700A. MS (ESI) m/e 234 (M+H)+.

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-bromomethyl-4-chloro-2-methoxy-benzene (705 mg), morpholine (0.52 mL, 6 mmol) in toluene (15 mL) was heated to 110° C. for 2 hours. The solution was then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum to provide 675 mg (93%) of the title compound. MS (ESI) m/e 242 (M+H)+. The solution was then partitioned between ethyl acetate and water The organic layer was washed with brine dried (MgSO4) filtered concentrated under vacuum

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-bromomethyl-4-chloro-2-methoxy-benzene (705 mg), morpholine (0.52 mL, 6 mmol) in toluene (15 mL) was heated to 110° C. for 2 hours. The solution was then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum to provide 675 mg (93%) of the title compound. MS (ESI) m/e 242 (M+H)+. The solution was then partitioned between ethyl acetate and water The organic layer was washed with brine dried (MgSO4) filtered concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Methyl imidazole (45 mg, 0.55 mmol) was dissolved in DMF. Sodium hydride (60 mg, 1.5 mmol) was added slowly. The mixture was stirred at room temperature until bubbling ceased. 1-Bromomethyl-4-chloro-2-methoxy-benzene (117 mg, 0.5 mmol) was added and the mixture was heated to 100° C. for 16 hours. The mixture was cooled to room temperature, diluted with ethyl acetate, and washed with water and with brine. The organic layer was dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel (1:1 hexanes/ethyl acetate) to provide 47 mg (40%) of the title compound. MS (ESI) m/e 237 (M+H)+. until bubbling the mixture was heated to 100° C. for 16 hours The mixture was cooled to room temperature washed with water and with brine The organic layer was dried (MgSO4) filtered concentrated under vacuum The residue was purified by flash column chromatography on silica gel (1:1 hexanes/ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Methyl imidazole (45 mg, 0.55 mmol) was dissolved in DMF. Sodium hydride (60 mg, 1.5 mmol) was added slowly. The mixture was stirred at room temperature until bubbling ceased. 1-Bromomethyl-4-chloro-2-methoxy-benzene (117 mg, 0.5 mmol) was added and the mixture was heated to 100° C. for 16 hours. The mixture was cooled to room temperature, diluted with ethyl acetate, and washed with water and with brine. The organic layer was dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel (1:1 hexanes/ethyl acetate) to provide 47 mg (40%) of the title compound. MS (ESI) m/e 237 (M+H)+. until bubbling the mixture was heated to 100° C. for 16 hours The mixture was cooled to room temperature washed with water and with brine The organic layer was dried (MgSO4) filtered concentrated under vacuum The residue was purified by flash column chromatography on silica gel (1:1 hexanes/ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Bromomethyl-4-chloro-2-methoxy-benzene (50 mg, 0.21 mmol), phenyl boronic acid (28 mg, 0.23 mmol), Pd(PPh3)4 (24 mg, 0.021 mmol) and K2CO3 (87 mg, 0.63 mmol) were combined in dioxane, purged with N2, and heated to reflux for 16 hours. The mixture was then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel eluting with 4:1 hexanes/ethyl acetate to provide 9 mg (18%) of the title compound. MS (ESI) m/e 233 (M+H)+. purged with N2 heated to reflux for 16 hours The mixture was then partitioned between ethyl acetate and water The organic layer was washed with brine dried (MgSO4) filtered concentrated under vacuum The residue was purified by flash column chromatography on silica gel eluting with 4:1 hexanes/ethyl acetate